When my best friend asked me to be her maid of honor, I had exactly two rules for the bachelorette: we all had to stay together, no scattering across hotel floors, and our home base had to put us minutes from both the Disney magic and a real night out. After far too many late-night group-chat debates, we booked a private vacation home at Windsor Hills Resort through Global Vacation Rentals. Honestly? It made the whole trip.
Here's exactly how our five days played out, where we ate, what we did, and the things I wish someone had told me before we went.
Why we picked Windsor Hills as our home base
Windsor Hills is a gated, 24-hour community of vacation homes sitting roughly two miles from the Walt Disney World main gate, you genuinely feel how close you are. We rented a five-bedroom house with its own screened private pool, which meant all of us under one roof, a kitchen big enough to actually cook in, and a backyard pool for the inevitable “we are NOT moving today” mornings.
A few things that sold me:
- The private pool. Worth every penny. Half our best moments happened right there with a speaker and a pitcher of something frozen.
- The resort water park. There's a big zero-entry lagoon-style pool with a slide and a hot tub at the community clubhouse, perfect for a low-key afternoon when nobody wants to commit to a theme park.
- The space. A clubhouse with a fitness center, a little movie theater, and games, plus close enough to Disney that park mornings weren't a slog.
If you're browsing, Global Vacation Rentals lists every home at Windsor Hills Resort here, 2-to-3-bedroom condos and townhomes for smaller groups, and big 5-to-6-bedroom houses with private pools if you're rolling deep like we were.
First night: a stunning dinner, then a lively walk
We flew in mid-afternoon, dropped our bags, and gave ourselves an hour at the house before getting ready. For night one I wanted something close but special, and Salt & The Cellar by Akira Back delivered.
It's a fine-dining spot from Michelin-starred chef Akira Back, tucked inside the stylish ette hotel just a few minutes from Windsor Hills. The room is sleek and grown-up, exactly the backdrop you want for the “she said yes to being our bride” toast. The Akira Back tuna pizza and the AB Wagyu tacos got passed around the table and vanished instantly, and the cocktail list (plus a genuinely thoughtful mocktail menu, so our non-drinking bridesmaid had something beautiful in her hand too) was a highlight. Fair warning: it's a treat-night kind of place, not an every-night one.
After dinner we drove ten minutes to the Promenade at Sunset Walk, an open-air district packed with restaurants, shops, and live music on an outdoor stage. We landed at The Wharf, an indoor-outdoor seafood spot and music hall, for one more round and a relaxed-but-buzzy end to the night.
Four ways we filled five days
We deliberately mixed high-energy nights with do-nothing pool time. Here's what made the cut.
1. “Drink Around the World” at EPCOT
The bachelorette classic. EPCOT's World Showcase is basically built for groups, you make your way around the country pavilions trying a drink from each. Heads up: it's an unofficial tradition (Disney doesn't sell it as a package), you just need regular park admission, and everyone has to be 21+. Pace yourselves and snack as you go.
2. A spa and cabana recovery day at Gaylord Palms
Our designated “treat ourselves” day. We rented a poolside cabana at the Gaylord Palms Resort and booked group treatments at the Relâche Spa, which puts together customizable bridal-party packages through their spa concierge. Ask about group perks when you book, they're set up for exactly this kind of crowd.
3. A big night out on International Drive
For our loudest night, we hit Howl at the Moon, a dueling-piano bar that runs actual bachelorette packages (reserved seating, line-skip, the whole bride-roast thing). Then we kept it going at Mango's Tropical Cafe nearby, Latin stage shows, dancing, full nightclub energy.
4. A sunset airboat ride (the surprise favorite)
The one everyone still texts about. We booked a private sunset airboat ride with Boggy Creek Airboat Adventures out in the wetlands south of the parks. Spotting alligators while the sky went pink over the marsh was the most Florida thing we did, and a gorgeous change of pace from the neon. (Confirm the private and sunset timing when you book; it's seasonal.)
The practical stuff I wish I'd known
- You need a rental car. Boggy Creek, the airport, and the spread-out attractions just aren't realistic without one.
- But rideshare your party nights. For International Drive and Sunset Walk, we split an Uber XL (fits about six) so everyone could drink and nobody fought over parking.
- Stock the house before you arrive. We scheduled a grocery delivery so the kitchen was ready when we walked in, no first-night supply run. There's a Walmart Supercenter on Highway 192 less than five minutes away and a Publix about three miles out.
- Time your trip. March through May and September through November are the sweet spots: warm but not brutal. Summer is hot and humid with near-daily afternoon thunderstorms (they blow through fast). Either way, book weekend nightlife and spa slots in advance.
- Build in a pool day. A private-pool home turns your recovery day into a highlight instead of dead time. Don't over-schedule.
The house that pulled it all together
I get asked for our exact home constantly, so here it is: we stayed at 7774 Basnett Circle, a five-bedroom, five-bath house at Windsor Hills that sleeps eleven. It has a private screened pool out back, a full kitchen, and enough bathrooms that ten women getting ready at once didn't turn into a war. It's rated a perfect five stars by past guests, and at roughly $230 a night for the entire home, split between us it came out to almost nothing.
If it's booked when you go, it's far from the only one, there's a whole range of top-rated Windsor Hills homes in the same pocket near Disney.
Would I do it again?
In a heartbeat. Having our own house at Windsor Hills meant the trip had a home, somewhere to spill back to at 1 a.m., make coffee in our robes, and relive the night before. It was close enough to Disney to feel like a parks trip and close enough to the bars to feel like a real getaway. Ten out of ten, would maid-of-honor again.
Ready to plan yours? Start with the homes at Windsor Hills Resort.